Lens adhesive, cemented lens, and imaging module

Patent metadata

Field	Value
Publication number	US-11518916-B2
Application number	US-202016912073-A
Country	US
Kind code	B2
Filing date	Jun 25, 2020
Priority date	Dec 26, 2017
Publication date	Dec 6, 2022
Grant date	Dec 6, 2022

Abstract

According to the present invention, a lens adhesive including a compound represented by General Formula 1 is provided.

Pol 1 -Sp 1 -L 1 -Ar-L 2 -Sp 2 -Pol 2   (General Formula 1)

In the formula, Ar is an aromatic ring group represented by General Formula 2-2 and the like.

In the formula, Z 1 and Z 2 each represent a hydrogen atom, a methyl group, and the like; A 1 and A 2 each represent —S— and the like; X represents C(Rz) 2 and the like (where Rz is a substituent, and two Rz's may form a ring); L 1 and L 2 each represent a single bond, —O—, —OC(═O)—, —OC(═O)O—, —OC(═O)NH—, and the like; Sp 1 and Sp 2 each represent a single bond or a linking group such as a linear alkylene group; Pol 1 and Pol 2 each represent a hydrogen atom or a polymerizable group; and a compound represented by General Formula 1 has at least one polymerizable group. Using the lens adhesive, it is possible to provide a cemented lens that is unlikely to deteriorate due to light, and an imaging module having high durability.

First claim

What is claimed is:

1. A lens adhesive comprising:
a compound represented by General Formula 1,
Pol 1 -Sp 1 -L 1 -Ar-L 2 -Sp 2 -Pol 2   (General Formula 1)

in General Formula 1, Ar is any of aromatic rings represented by General Formulas 2-1 to 2-4,

in the formulas, Q 1 represents —S—, —O—, or NR 11 —, where R 11 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms,
Y 1 represents an alkyl group which has 1 to 6 carbon atoms and may have a substituent, an aromatic hydrocarbon group which has 6 to 12 carbon atoms and may have a substituent, or an aromatic heterocyclic group which has 3 to 12 carbon atoms and may have a substituent,
Z 1 , Z 2 , and Z 3 each independently represent a hydrogen atom, an aliphatic hydrocarbon group which has 1 to 20 carbon atoms and may have a substituent, an alkoxy group which has 1 to 20 carbon atoms and may have a substituent, an alicyclic hydrocarbon group which has 3 to 20 carbon atoms and may have a substituent, a monovalent aromatic hydrocarbon group which has 6 to 20 carbon atoms and may have a substituent, a halogen atom, a cyano group, a nitro group, —NR 12 R 13 , or SR 12 , where Z 1 and Z 2 may be bonded to each other to form an aromatic hydrocarbon ring which may have a substituent or an aromatic heterocyclic ring which may have a substituent, and R 12 and R 13 each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms,
A 1 and A 2 each independently represent a group selected from the group consisting of —O—, —NR 21 —, —S—, and CO—, where R 21 represents a hydrogen atom or a substituent,
X represents O, S, C to which a hydrogen atom or a substituent is bonded, or N to which a hydrogen atom or a substituent is bonded,
Ax represents an organic group which has 1 to 30 carbon atoms and has at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocyclic ring; and Ay represents a hydrogen atom, an alkyl group which has 1 to 6 carbon atoms and may have a substituent, or an organic group which has 1 to 30 carbon atoms and has at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocyclic ring, where the aromatic ring included in Ax and Ay may have a substituent, and Ax and Ay may be bonded to each other to form a ring which may have a substituent,
Q 2 represents a hydrogen atom, or an alkyl group which has 1 to 6 carbon atoms and may have a substituent,
L 1 and L 2 each independently represent a single bond, or a linking group selected from the group consisting of —O—, —S—, —C(═O)—, —OC(═O)—, —C(═O)O—, —OC(═O)O—, —NR 101 C(═O)—, —C(═O)NR 102 —, —OC(═O)NR 103 —, —NR 104 C(═O)O—, —SC(═O)—, and C(═O)S—, where R 101 , R 102 , R 103 , and R 104 each independently represent -Sp 3 -Pol 3 or a halogen atom,
Sp 1 and Sp 2 each represent a single bond, or a linking group selected from the group consisting of a linear alkylene group which has 1 to 30 carbon atoms and may have a substituent, and a group in which one or two or more non-adjacent —CH 2 —'s are substituted by —O—, —S—, —C(═O)—, —OC(═O)—, —C(═O)O—, —OC(═O)O—, —NR 201 C(═O)—, —C(═O)NR 202 —, —OC(═O)NR 203 —, —NR 204 C(═O)O—, —SC(═O)—, or —C(═O)S— in a linear alkylene group which has 2 to 30 carbon atoms and may have a substituent, where R 201 , R 202 , R 203 , and R 204 each independently represent -Sp 4 -Pol 4 or a halogen atom,
Sp 3 and Sp 4 each independently represent a single bond or a divalent linking group, and
Pol 1 , Pol 2 , Pol 3 , and Pol 4 each independently represent a hydrogen atom or a polymerizable group, and
wherein the compound represented by General Formula 1 has at least one polymerizable group.

2. The lens adhesive according to claim 1 , wherein the lens adhesive includes a polymer having an ethylenically unsaturated group.

3. A method of producing a cemented lens comprising adhesion of two or more lenses using the lens adhesive according to claim 1 .

4. The method according to claim 3 , wherein Ar is an aromatic ring represented by General Formula 2-2.

5. The method according to claim 3 , wherein any of L 1 or L 2 is —O—, —OC(═O)—, —OC(═O)O—, or O—C(═O)NH—.

6. The method to claim 3 , wherein any of L 1 or L 2 is —O—; and any of Sp 1 or Sp 2 is a linking group selected from the group consisting of a linear alkylene group which has 1 to 30 carbon atoms and may have a substituent, and a group in which one or two or more non-adjacent —CH 2 —'s are substituted by —O—, —S—, —C(═O)—, —OC(═O)—, —C(═O)O—, —OC(═O)O—, —NR 201 C(═O)—, —C(═O)NR 202 —, —OC(═O)NR 203 —, —NR 204 C(═O)O—, —SC(═O)—, or —C(═O)S— in a linear alkylene group which has 2 to 30 carbon atoms and may have a substituent and in which a terminal on an L 1 side or an L 2 side is —CH 2 —.

Assignees

• Fujifilm Corp

Inventors

• Nakayama Takafumi
• Shiraiwa Naozumi
• Morooka Naoyuki

Classifications

• C08F220/1808

  C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (meth)acrylate · CPC title

• G02B3/00

  Simple or compound lenses · CPC title

• C08F279/02

  on to polymers of conjugated dienes · CPC title

• C07D277/82

  Nitrogen atoms · CPC title

• C07D417/04

  directly linked by a ring-member-to-ring-member bond · CPC title